Synthesis, spectral, magnetic, DFT calculations, antimicrobial studies and phenoxazinone synthase biomimetic catalytic activity of new binary and ternary Cu(II), Ni(II) and Co(II) complexes of a tridentate ONO hydrazone ligand

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A new hydrazone ligand 4,6‐bis(2‐hydroxynaphthalen‐1‐yl)methyl‐ene)hydrazono)ethyl)benzene‐1,3‐diol (H4L; DHNAPH) was synthesized by the reaction of 4,6‐bis(1‐hydrazonoethyl)benzene‐1,3‐diol (NH2DAR) with 2‐hydroxy 1‐naphthaldehyde. Co (II), Ni (II), and Cu (II) complexes ([M2L(H2O)6].nH2O.mEtOH (M = Co, Ni or Cu; n = 0.5 or 1; and m = 0.5 or 0) of DHNAPH have been successfully synthesized. Characterization of DHNAPH and its complexes was performed by analytical, spectral (infrared [IR], mass, UV–Vis, 1H NMR, and electron spin resonance [ESR]), powder X‐ray diffraction (XRD), magnetic susceptibility, molar conductivity, and thermal gravimetric analysis (TGA) techniques. The analytical data, magnetic moments, and spectral studies recognized octahedral geometries for DHNAPH complexes. DHNAPH acts as a bis (dibasic tridentate) via (C=N azomethine and 2 OH) with metal in complexes. The XRD patterns for DHNAPH and its complexes indicate crystalline nature of DHNAPH and its Cu complex. DHNAPH has triclinic system, while copper‐DHNAPH has a tetragonal system with different unit cell parameters. Theoretical studies showed that there is a good relation between experimental IR data and theoretical calculation. The activity of DHNAPH and its complexes against Hepatocellular carcinoma, fungi, and bacteria has been tested. The new complexes are more active than DHNAPH, and the highest antitumor activity was given by copper (II) complex, which showed lower IC50 than that of Cisplatin. The DNA binding of DHNAPH and Cu‐DHNAPH has been investigated. Molecular docking studies showed that all the tested compounds show good binding scores revealing good fitting in between the DNA strands. There is an agreement between docking data and DNA binding results.

Section: Electronic Spectra and Magnetic Moment Measurementsmentioning

confidence: 75%

Section: Resultsmentioning

confidence: 99%

Co (II), Ni (II), and Cu (II) complexes of 4,6‐bis(2‐hydroxynaphthalen‐1‐yl)methyl‐ene)hydrazono)ethyl)benzene‐1,3‐diol: Synthesis, spectroscopic, biological, and theoretical studies

Samy

2022

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“…[97] These results indicate that the complexation of copper(II) to hydrazone ligands is an effective strategy to improve the biological properties of the free ligand, as reported previously for similar compounds. [23,27,[98][99][100]…”

Section: Antimicrobial Activitymentioning

confidence: 99%

A binuclear copper(II) complex based on hydrazone ligand: Characterization, molecular docking, and theoretical and antimicrobial investigation

Santiago

Duarte

Nascimento

et al. 2021

A new binuclear copper(II) complex [Cu 2 L 2 (μ-SO 4 )(dmf)] with the 2-acetylpyridinebenzoylhydrazone (HL) ligand was synthesized and characterized by elemental analysis, Fourier transform infrared (FT-IR), ultravioletvisible (UV-Vis), single-crystal X-ray diffraction, density functional theory (DFT), and molecular docking studies. The crystal structure revealed each copper(II) atom coordinated to the NNO chelating system of the anionic hydrazone ligand and a sulfate bridged. The copper ions are connected by a sulfate bridge, which keeps a distance of 3.292(3) Å between the two copper(II) centers. Additionally, only one of the copper(II) atoms is coordinated to the oxygen atom of the N,N-dimethylformamide (dmf) solvent molecule, resulting in two different geometry to each metal center. CuÁÁÁO interactions are observed for the secondary coordination sphere of Cu1 and Cu2 atoms with distances of 2.545(2) and 2.821(3) Å, respectively. Theoretical studies with DFT were performed to optimize the geometry of the complex and investigate its spectroscopic properties supporting the experimental results. Two different approaches were used in computational calculations, the plane wave using Perdew-Burke-Ernzerhof (PBE) functional and the localized basis set using the following functionals: B3LYP, B3PW91, CAM-B3LYP, LC-wPBE, M06-2X, ωB97-XD, PBE1PBE, and HSEH1PBE. The in vitro antibacterial potential of the new complex was evaluated against pathogenic bacteria and fungi and compared with the free ligand. The molecular docking was used to predict the inhibitory activity of the ligand and complex against one Gram-positive bacteria (Enterococcus faecalis), one Gram-negative bacteria (Enterobacter aerogenes), and one fungi (Candida albicans) species.

“…A large number of scientists reported synthesis and spectroscopic characterisation of mixed‐ligand complexes as well as their different potential applications. [ 1–10 ] Furthermore, it has been concluded that the presence of a nitrogen donor heterocyclic ligand, for example, 1,10‐phenanthroline or 2,2′‐bipyridine improves the biological activity of the metal complexes. [ 11–14 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterisation and biological activities of mixed ligand oxovanadium (IV) complexes derived from N,N‐diethyl‐N′‐para‐substituted‐benzoylthiourea and hydrotris(3,5‐dimethylpyrazolyl)borate

Al‐abbasi

Tahir

Kayed

et al. 2022

A series of oxovanadium (IV) complexes namely, [Tp*VOL1], [Tp*VOL2], [Tp*VOL3], [Tp*VOL4] and [Tp*VOL5] (where Tp = hydrotris(3,5‐dimethylpyrazolyl)borate, HL1 = 1‐benzoyl‐3,3‐diethylthiourea, HL2 = 1‐(4‐chlorobenzoyl)‐3,3‐diethylthiourea, HL3 = 1,1‐diethyl‐3‐(4‐methoxybenzoyl)thiourea, HL4 = 1,1‐diethyl‐3‐(4‐nitrobenzoyl)thiourea, HL5 = N‐(diethylcarbamothioyl)biphenyl‐4‐carboxamide) were prepared and characterised on the basis of mass spectrometry, elemental analysis and spectroscopy techniques (IR, UV–Vis and electron paramagnetic resonance, EPR) and mass spectrometry. The crystal structure of [Tp*VOL3] was elucidated from single crystal X‐ray diffraction study and the crystals adopted a triclinic system with a P‐1 (Z = 2) space group and unit cell parameters of a = 10.4953(4), b = 11.5290(5) and c = 15.0656(7) Å. The cyclic voltammetry showed a reversible oxidation of V (IV)/V(V) at about 0.50 V (vs Fc+/Fc). The HOMO and LUMO of benzoylthiourea were established by theoretical calculation based on DFT level using B3LYP method and a double numeric plus polarisation (DNP) basis set. The in vitro tests for antimicrobial activity showed that the complexes have a moderate inhibitory effect. The complex [Tp*VOL1] exhibited cytotoxic activity against the human hepatocellular carcinoma cell line (HepG2) at the concentration of 20 mg ml−1. However, no cytotoxic activity was observed against the Chang liver cells.